Hydrochloric Acid → 6-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

HRID 732830Notes

Reaction equation

HRID 732830 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.Br[C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[C:8]([C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[CH:7]=[CH:6]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 141126-Methoxy-alpha-tetraloneHCID 660374-BromothioanisoleHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 685188176-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Place 6-methoxy-1-tetralone (1 eq.), 4-bromothioanisole (2.5 eq.), palladium acetate (0.01 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.02 eq.) and toluene in a 3 neck flask equipped with a mechanical stirrer, reflux condenser, nitrogen purge and a temperature probe. Add sodium tert-butoxide (4 eq.) and heat the slurry to reflux. After about 2-4 hours, cool the reaction to room temperature and add 3M aqueous HCl along with tetrahydrofuran. Stir the biphasic reaction mixture for 30 minutes before filtration and separation of the layers. Concentrate the organic layer to isolate 6-methoxy-2-(4-methylthiophenyl)naphthalene-1-ol by filtration.

Workup

  1. temperaturereflux condenser
  2. customnitrogen purge
  3. temperatureto reflux
  4. temperaturecool
  5. customthe reaction to room temperature
  6. customthe biphasic reaction mixture for 30 minutes
  7. filtrationbefore filtration and separation of the layers
  8. concentrationConcentrate the organic layer

Sources & evidence

ORD record
ord-26de4d369cb74903adda9276724dd92a
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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